Derivatives of alpha-alkyl polyolefinic carboxylic acid useful in the treatment of psoriasis

Abstract

This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R 1 , R 2 , R 3 , R 4 , n and m are defined within.

What is claimed is: 
     
       1. Compounds of the structure ##STR8## wherein n is 0 to 3, m is 0 to 1, and   R 1  and R 4  are each independently hydrogen or an alkyl group of from 1 to 5 carbon atoms;   R 2  is an alkyl group of from 1 to 5 carbon atoms;   R 3  is ##STR9##  retinoyloxy, or ##STR10## R 5  is independently H, C 1  -C 20  alkyl, aryl, aralkyl, and Z is a cycloalkyl, cycloalkenyl or cyclodialkenyl group substituted with from 0 to 5 C 1  -C 5  alkyl groups, a keto group or a hydroxyl group, or a phenyl group substituted with from 0 to 4 hydroxy, C 1  -C 5  alkoxy, C 1  -C 5  alkyl or trifluoromethyl groups or halogen atoms or combinations thereof; and the pharmaceutically-acceptable salts thereof.   
     
     
       2. A compound of claim 1 wherein R 1  and R 2  are methyl, and when R 4  is present, R 4  is methyl. 
     
     
       3. A compound of claim 1 wherein Z is cycloalkenyl, cyclodialkenyl or phenyl group substituted with 1-4 methyl groups and, optionally, a C 1  -C 5  alkoxy group. 
     
     
       4. A compound of claim 3 wherein Z is 2,6,6-trimethyl-1-cyclohexen-1-yl;   4-methoxy-2,3,6-trimethylphenyl;   2,6,6-trimethyl-2-cyclohexen-1-yl or   2,6,6-trimethyl-1,3-cyclohexadien-1-yl.   
     
     
       5. A compound of claim 3 having the structure ##STR11## 
     
     
       6. A pharmaceutical composition for the treatment of psoriasis in a human host which comprises, in combination with at least one pharmaceutically acceptable extender, an effective amount of a compound of claim 1. 
     
     
       7. 2,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)2,4,6,8,10-undecapentaenyl acetate. 
     
     
       8. 2,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl palmitate. 
     
     
       9. 2,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl retinoate. 
     
     
       10. 2,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate. 
     
     
       11. 2,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenyl palmitate.